Pentane → 3,3-Dimethyl-7-iso-propyl-2,3-dihydro-benzofuran-5-boronic acid

HRID 2085574Notes

Reaction equation

HRID 2085574 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:13]([CH3:15])[CH3:14])[C:5]2[O:9][CH2:8][C:7]([CH3:11])([CH3:10])[C:6]=2[CH:12]=1.C([Li])(C)(C)C.CCCCC.[B:26](OC)([O:29]C)[O:27]C>O1CCCC1>[CH3:10][C:7]1([CH3:11])[C:6]2[CH:12]=[C:2]([B:26]([OH:29])[OH:27])[CH:3]=[C:4]([CH:13]([CH3:15])[CH3:14])[C:5]=2[O:9][CH2:8]1

Participants

6

Reactant 4

HCID 8003PentaneHCID 8470Trimethyl borateHCID 154540775-Bromo-3,3-dimethyl-7-isopropyl-2,3-dihydro-benzofuranHCID 178418306HCID 178418306, compound

Product 1

HCID 227313033,3-Dimethyl-7-iso-propyl-2,3-dihydro-benzofuran-5-boronic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following General Procedure A and using 5-bromo-3,3-dimethyl-7-iso-propyl-2,3-dihydro-benzofuran (0.8 g, 3 mmol), 15 mL of anhydrous tetrahydrofuran, 1.7M solution of t-butyllithium in n-pentane (3.53 mL, 6 mmol) and trimethyl borate (0.75 mL, 6 mmol), the title compound was obtained as a foam that was used as such for the next step without purification and characterization. 5-Bromo-3,3-dimethyl-7-iso-propyl-2,3-dihydro-benzofuran can be prepared as described in U.S. Pat. No. 6,093,838.

Sources & evidence

ORD record
ord-124d582de8f34d99a4bc13b98bf27216
Source dataset
uspto-grants-2004_04
Patent number
US06720423B2

Reaction notes

Loading…